title: [[(tert-Butyl)dimethylsilyl]oxy]methyl group for sulfur protection.
abstract: Aromatic and aliphatic thiols can be protected by reaction with t-BuMe(2)SiOCH(2)Cl in DMF in the presence of a base (2,6-lutidine or proton sponge); the resulting t-BuMe(2)SiOCH(2)SR or t-BuMe(2)SiOCH(2)SAr are deprotected by sequential treatment with Bu(4)NF and I(2) to give symmetrical disulfides. Another mode of deprotection involves reaction with a sulfenyl chloride; this process gives an unsymmetrical disulfide and was examined with Me(CH(2))(11)SCH(2)OSiMe(2)Bu-t and three sulfenyl chlorides.
authors.affiliation: Chemistry Department, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
authors.forename: Lihong
authors.initials: L
authors.lastname: Wang
authors.forename: Derrick L J
authors.initials: DL
authors.lastname: Clive
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis; D008745:Methylation; D015394:Molecular Structure; D010087:Oxides / Q000737:chemistry*; D013455:Sulfur / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D006576:Heterocyclic Compounds, 4 or More Rings; C493112:MPC1001; D010087:Oxides; D013455:Sulfur